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SMB00075

Sigma-Aldrich

(−)-Arctigenin

≥95% (LC/MS-ELSD)

Synonym(s):

2(3H)-Furanone, (3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone

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About This Item

Empirical Formula (Hill Notation):
C21H24O6
CAS Number:
7770-78-7
Molecular Weight:
372.41
MDL number:
MFCD00870597
UNSPSC Code:
12352205
PubChem Substance ID:
329824754
NACRES:
NA.25

Assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

COc1cc(C[C@@H]2[C@H](COC2=O)Cc3ccc(OC)c(OC)c3)ccc1O

InChI

1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1

InChI key

NQWVSMVXKMHKTF-JKSUJKDBSA-N

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General description

Arctigenin is a lignan found in the root of Arctium lappa L. It has been used in pharmacologic, as well as cosmetic, research and has demonstrated several antiviral and anticancer effects.

Biochem/physiol Actions

Dibenzylbutyrolactone ligand, natural product, viral integrase and topoisomerase II inhibitor, antioxidant, antiviral, anti-inflammatory, immunomodulator.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
12222867V
122228-67V

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Min Kyung Cho et al.
International immunopharmacology, 4(10-11), 1419-1429 (2004-08-18)
Arctigenin, naturally occurring in Bardanae fructus, Saussurea medusa, Arctium lappa L., Torreya nucifera and Ipomea cairica, is a phenylpropanoid dibenzylbutyrolactone lignan with antioxidant and anti-inflammatory activities. Previously, we showed that arctigenin potently inhibited the induction of nitric oxide synthase (iNOS)
Jong-Sik Jin et al.
Biological & pharmaceutical bulletin, 30(5), 904-911 (2007-05-03)
Plant lignans, such as pinoresinol diglucoside, secoisolariciresinol diglucoside and arctiin, are metabolized to mammalian lignans, enterolactone or enterodiol, by human intestinal bacteria. Their metabolic processes include deglucosylation, ring cleavage, demethylation, dehydroxylation and oxidation. Here we isolated an intestinal bacterium capable
Xianjuan Kou et al.
International immunopharmacology, 11(8), 1095-1102 (2011-03-24)
Arctigenin has been demonstrated to have an anti-inflammatory function, but the precise mechanisms of its action remain to be fully defined. In the present study, we determined the effects of arctigenin on lipopolysaccharide (LPS)-induced production of proinflammatory mediators and the
Ju-Young Kim et al.
Journal of cellular physiology, 224(1), 33-40 (2010-03-17)
Cancer cells in poorly vascularized solid tumors are constantly or intermittently exposed to stressful microenvironments, including glucose deprivation, hypoxia, and other forms of nutrient starvation. These tumor-specific conditions, especially glucose deprivation, activate a signaling pathway called the unfolded protein response
Xiangyang Yao et al.
Journal of cellular biochemistry, 112(10), 2837-2849 (2011-05-25)
Arctigenin is a dibenzylbutyrolactone lignan isolated from Bardanae fructus, Arctium lappa L, Saussureamedusa, Torreya nucifera, and Ipomea cairica. It has been reported to exhibit anti-inflammatory activities, which is mainly mediated through its inhibitory effect on nuclear transcription factor-kappaB (NF-κB). But
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